Iodine → 2,3,4,5-Tetrahydro-alpha-methyl-1-benzoxepine-8-methanol

HRID 373549

Reaction equation

HRID 373549 reaction equation
Br[C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1.II.[O:15]1CC[CH2:17][CH2:16]1>BrCCBr>[CH3:17][CH:16]([C:2]1[CH:12]=[CH:11][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:4]=2[CH:3]=1)[OH:15]

Participants

5

Reactant 3

HCID 807IodineHCID 8028TetrahydrofuranHCID 199355348-Bromo-2,3,4,5-tetrahydrobenzo[b]oxepine

Product 1

HCID 199354272,3,4,5-Tetrahydro-alpha-methyl-1-benzoxepine-8-methanol

Reagents, catalysts & solvents 1

HCID 78391,2-DibromoethaneCatalyst

Conditions

Temperature
-10 °C

Procedure

7.3 g of 8-bromo-2,3,4,5-tetrahydro-1-benzoxepine in 30 ml of absolute tetrahydrofuran were added under argon to 930 mg shavings and a granule of iodine. The reaction was intitiated by the addition of a few drops of 1,2-dibromoethane and has finished after 2 hours. Thereafter, the reaction mixture was cooled to -10° C. and excess acetaldehyde was distilled into the reaction vessel. After 10 minutes, the mixture was hydrolyzed with saturated sodium bicarbonate (NaHCO3) solution, extracted with ether, washed with water, dried and evaporated to dryness. Chromatography on silica gel (petroleum ether/ethyl acetate 3:1) yielded 4.93 g of 2,3,4,5-tetrahydro-α-methyl-1-benzoxepine-8-methanol as a colorless oil.

Workup

  1. distillationexcess acetaldehyde was distilled into the reaction vessel
  2. waitAfter 10 minutes
  3. extractionextracted with ether
  4. washwashed with water
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-c8c67de915d2404f9289478b5992c195
Source dataset
uspto-grants-1992_11
Patent number
US05164387

Linked notes

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